Fluoroalcohol bactericides



United States Patent ce Pate, Feitifiti:

by acid hydrolysis. This process can be illustrated further 3 495 017 bthe e nations set forth below: FLUoRoALcoHoi BACTERICIDE i C q U OM BrArleen C. Pierce, Monmouth Junction, NJ., assignor to i 2 g AlliedChemical Corporation, New York, N.Y., a cor- 0:0 CHg=OHMgBr poration ofNew York 5 YF YF \CH:CH No Drawing. Filed Sept. 15. 1967, Ser. No.668,171 2 2 2 Int. Cl. A61k 27/00; C07C 33/10 H2O OMgB, Xmc 0H U.S. Cl.424-343 4 'Clalms aoitLHzO C 10 YFQC/ oH=cH2 YF2C CH=CH2 ABSTRACT OF THEDISCLOSURE This specification discloses a method of combatingcomposition and methods for preparing them have been micro-organisms,particularly Staphylococcus aureus cells, disclosed in greater detail ina copending US. application by treating them with an effective amount ofan ethylof Dear and Gilbert, Ser. No. 550,113, filed May 16, enicallyunsaturated fluorine-containing aliphatic alcohol 1966. in vapor phase.In accordance with the invention, the subject fiuoroalcohols can beintroduced into the area to be sterilized The usual methods ofsterilization, such as use of in hquie form and hhewed to penetrate areah steam, heat, chemical solution, radiation, and the like, h eAlterhahvely they can he admlxed h are often impractical when largeareas such as hospital dhueht Inert gas or mlxture h h an example rooms,laboratories, and animal quarters are to be sterican be bubbled throughthe e shhleet fiuoroalcohols lized. This may be true also whensterilization of articles and the huoroaleohel'ladeh Passed mm the mealto which may adversely afiected by moisture or heat, be treated. TheSUbJCClI fiuoroalcohol can also be adsuch as delicate laboratory andmedical equipment, or hhxed Wlth Sultahle Propelleht hhxture h fabrics,plastics, and the like, are required. Sterilization mm t area' Theehhleet fiuoroalcohols mdlvlduahy problems of this kind can frequentlybe overcome by or h h 9 y of can h empleyed as h using chemicalantimicrobial agents which are effective achve lhgredleht 1h eemhahhgrhleroorgahlsms or If in vapor phase to produce sterilization. Effectivevapor deslred h h e can he used Wlth other khowh vapor phase chemicalantimicrobial agents must be capable of ee ahhmlerohlal ,agehts such hethylene oxlde' In being readily introduced into the area to be treated;of addition to a vapor diluent, the sub ect fiuoroalcohols can rapidlyand thoroughly penetrating all porous surfaces he used Wlth othervaponzehle eompohehts Such as in the area; of effectively penetratingthe micro-organisms Perfumes deoderahts e vapor and the to be treatedand of controlling them, i.e. by destroying e khhwh the e the dosages ofa ehemleal them or by inhibiting their propagation at normalantimicrobial agent required to effect control can vary peratures andrelative humidities; and of being readily Wldely depehdlhg P theParticular mlcroorgamsms, to removed by aeration. Chemical compositionswhich can e h e h the area to be treated the h meet these stringentrequirements are relatively few and wlthlh Whleh 13 deslred to effectcontrol he thus the use of vapor phase antimicrobial agents has hadmental eohchhohs e as temperature hh i butlimited use up to the presenttime. 40 etc. Generally, as with other vapor phase antimicrob alAccording to the method of the present invention, agents e effeehvehesse the eubleet huemaleohols microorganisms can be controlled by treatingthem with creases Wlth an Increase, h relahve h In the an effectiveamount of an unsaturated fluoroalcohol havferred method of practlcmg hlnYentlon Water Vapor ing the structural formula: is present in the areato be sterillzed in an amount equivalent to at least about 90% relativehumidity when the subject fluoroalcohol vapor is introduced. Asufiicient amount of the subject fluoroalcohol is employed so as XF2C\to provide the desired toxicity. The dosages that will be 0 required tosterilize a particular area to ensure control YF2C/ of microorganismscan be readily ascertained, as will be known to one skilled in the art.

The following examples will serve to further illustrate wherein X and Yare the same or diflerent and represent h ihvention i h to be understood e the invenhydrogen, fluoroine and chlorine in Vapor Phase. tion isnot to be hmited to the details described therein.

Examples of suitable unsaturated fiuoroalcohols en- In the exampies allparts and Percentages are by weight compassed within this generalformula are: unless otherwlse noted1,1,1-trifluoro-2-trifiuoromethyl-3-buten-2-ol, EXAMPLE 11,1,1-chlorofiuoro-2-trifluoromethyl-3-buten-2-ol, Preparation of 1,l,1-trifiuoro-2-trifiuoromethyl-3-1,1,1-chlorodifi-uoro-2-chlorodifiuoromethyl-3- 0 buten-2-ol buten-2-ol,1,171 trifluom 2 difluoromethyl 3 buten z ol 62 5 parts of vinylmagnesium chloride prepared ac- 1,1,1 chlomdifiuoro z difiuoromethyl 3buten 2 OL cording to the procedure given by H. E. Ramsden et a1., y 3 21, Org. Chem., 22, ll'l ml. Of tetrahydro- 6 furan was charged to avessel fitted with a stirrer, gas

and the like and isomers thereof. inlet tube, nitrogen purge,thermometer and Dry-Ice/ The unsaturated fiuoroalcohols used in theinvention methylene chloride condenser. The vessel was cooled to andhereinafter referred to as the subject fiuoroalcohols, about 5 C. and116 parts of hexafluoroacetone were can be prepared by reacting anappropriate fiuoroacetone added over a two-hour period. Stirring wascontinued with a vinyl organometallic compound, such as vinyl overnightat room temperature. The mixture was then magnesium chloride, vinylmagnesium bromide and vinyl cooled to 5 C. and 270 parts of a 10%hydrochloric lithium, in a solvent such as tetrahydrofuran, followedacid aqueous solution were stirred in. The layers which wherein X and Yhave the meanings given above. These EXAMPLE 2 One-tenth ml. portions of1,1,1-trifiuoro 2 trifiuoromethyl-3-buten-2-ol, as prepared above, werecharged to one-liter flasks containing air having a predeterminedrelative humidity. Circular patches of cotton cloth, each having an areaof about 2 cm. and impregnated with an aqueous suspension of about 5 10Staphylococcus aureus cells and subsequently dried, were suspended bywires about halfway down into the flasks. The flasks were stoppered andthe contaminated patches were exposed to the fiuoroalcohol vapor forperiods of 1, 4 and 24 hours. At the end of the exposure periods, thepatches were removed and assayed for viable organisms by the pourplatemethod as follows: the patches were placed in dilution blanks composedof aqueous solutions of 0.1% by volume of lecithin and 0.71% of asuitable emulsifier which in this case was a polyoxyethylene derivativeof fatty acid partial esters of hexitol anhydrides available as Tween 80from Atlas Powder Company and the solucentage of organisms killed by thetest fiuoroalcohol was" calculated by comparison of the number foundafter ex; posure with an assay of unexposed contaminated patches.Bacteria counts were made with a Quebec Colony counter.

After one hours exposure to1,1,-1-trifiuoro-2-trifiuoromethyl-3-buten-2-ol vapor at 72% relativehumidity, over 99.9% of the Staphylococcus .aureus cells were killed.At'

90% relative humidity, 100% of the cells were killed after one hoursexposure to the test fiuoroalcohol.

4 EXAMPLES 3-4 The procedure as in Example 2 is repeated using 1,1,1-chlorodifiuoro-2-trifluoromethyl-3-buten 2 01 and 1,1,1-trifluoro-2-difiuoromethyl-3-buten-2-ol prepared according to theprocedure set forth in Example 1 but substitutingchloropentafiuoroacetone and pentafluoroacetone respectively forhexafiuoroacetone. A comparable bactericidal efiect is noted.

It will be apparent that many modifications and variations may beeffected without departing from the scope of the novel concepts of thepresent invention, and the illustrative details disclosed are not to beconstrued as imposing limitations on the invention.

I claim:

1. A method for combating bacteria which comprises treating saidbacteria with an eifective amount of an unsaturated fiuoroalcohol havingthe formula:

wherein X and Y can be the same or dilferent and are selectedfrom thegroup consisting of hydrogen, fluorine and chlorine, in vapor phase.

2. A method according to claim 1 wherein said fiuoroalcohol is employedin the presence of water vapor.

3. A method according to claim 2 wherein said fluoroalcohol is1,l,1-trifluoro-2-trifluoromethyl-3-buten-2-ol.

4. A method according to claim 2 wherein said microorganisms areStaphylococcus aureus cells.

References Cited UNITED STATES PATENTS ALBERT T. MEYERS, PrimaryExaminer A HOWARD M. ELLIS, Assistant Examiner Us. 01. X.R. 260-633

